JPH11500712A - 疎水性タキサン誘導体 - Google Patents
疎水性タキサン誘導体Info
- Publication number
- JPH11500712A JPH11500712A JP8521801A JP52180196A JPH11500712A JP H11500712 A JPH11500712 A JP H11500712A JP 8521801 A JP8521801 A JP 8521801A JP 52180196 A JP52180196 A JP 52180196A JP H11500712 A JPH11500712 A JP H11500712A
- Authority
- JP
- Japan
- Prior art keywords
- group
- formula
- taxane derivative
- integer
- zero
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Ceased
Links
- DKPFODGZWDEEBT-QFIAKTPHSA-N taxane Chemical class C([C@]1(C)CCC[C@@H](C)[C@H]1C1)C[C@H]2[C@H](C)CC[C@@H]1C2(C)C DKPFODGZWDEEBT-QFIAKTPHSA-N 0.000 title claims abstract description 110
- 230000002209 hydrophobic effect Effects 0.000 title abstract description 39
- 150000002632 lipids Chemical class 0.000 claims abstract description 58
- 229940123237 Taxane Drugs 0.000 claims abstract description 46
- 238000000034 method Methods 0.000 claims abstract description 46
- 241001465754 Metazoa Species 0.000 claims abstract description 32
- 239000000203 mixture Substances 0.000 claims abstract description 31
- 206010028980 Neoplasm Diseases 0.000 claims abstract description 17
- 239000002502 liposome Substances 0.000 claims description 53
- 230000001093 anti-cancer Effects 0.000 claims description 13
- 239000012867 bioactive agent Substances 0.000 claims description 12
- -1 complex Substances 0.000 claims description 12
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 11
- 239000000194 fatty acid Substances 0.000 claims description 11
- 229930195729 fatty acid Natural products 0.000 claims description 11
- 201000011510 cancer Diseases 0.000 claims description 9
- 230000037396 body weight Effects 0.000 claims description 6
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims description 5
- 201000005202 lung cancer Diseases 0.000 claims description 4
- 208000020816 lung neoplasm Diseases 0.000 claims description 4
- 206010006187 Breast cancer Diseases 0.000 claims description 3
- 208000026310 Breast neoplasm Diseases 0.000 claims description 3
- 206010009944 Colon cancer Diseases 0.000 claims description 3
- 102000004895 Lipoproteins Human genes 0.000 claims description 3
- 108090001030 Lipoproteins Proteins 0.000 claims description 3
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- 206010061535 Ovarian neoplasm Diseases 0.000 claims description 2
- 206010060862 Prostate cancer Diseases 0.000 claims description 2
- 210000004556 brain Anatomy 0.000 claims description 2
- 210000001072 colon Anatomy 0.000 claims description 2
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- 239000000693 micelle Substances 0.000 claims description 2
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- 239000012615 aggregate Substances 0.000 claims 1
- 125000005313 fatty acid group Chemical group 0.000 claims 1
- 229960001592 paclitaxel Drugs 0.000 description 62
- 229930012538 Paclitaxel Natural products 0.000 description 59
- RCINICONZNJXQF-MZXODVADSA-N taxol Chemical compound O([C@@H]1[C@@]2(C[C@@H](C(C)=C(C2(C)C)[C@H](C([C@]2(C)[C@@H](O)C[C@H]3OC[C@]3([C@H]21)OC(C)=O)=O)OC(=O)C)OC(=O)[C@H](O)[C@@H](NC(=O)C=1C=CC=CC=1)C=1C=CC=CC=1)O)C(=O)C1=CC=CC=C1 RCINICONZNJXQF-MZXODVADSA-N 0.000 description 59
- 125000000962 organic group Chemical group 0.000 description 28
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 19
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 19
- 239000003814 drug Substances 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 13
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- 210000004027 cell Anatomy 0.000 description 12
- 150000004665 fatty acids Chemical class 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 9
- 239000002609 medium Substances 0.000 description 8
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- SUHOOTKUPISOBE-UHFFFAOYSA-N O-phosphoethanolamine Chemical compound NCCOP(O)(O)=O SUHOOTKUPISOBE-UHFFFAOYSA-N 0.000 description 6
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
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- NRJAVPSFFCBXDT-HUESYALOSA-N 1,2-distearoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCCCCCCCCCCC NRJAVPSFFCBXDT-HUESYALOSA-N 0.000 description 5
- 238000005481 NMR spectroscopy Methods 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
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- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Natural products C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 5
- WTJKGGKOPKCXLL-RRHRGVEJSA-N phosphatidylcholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCC=CCCCCCCCC WTJKGGKOPKCXLL-RRHRGVEJSA-N 0.000 description 5
- 229950004354 phosphorylcholine Drugs 0.000 description 5
- PYJNAPOPMIJKJZ-UHFFFAOYSA-N phosphorylcholine chloride Chemical compound [Cl-].C[N+](C)(C)CCOP(O)(O)=O PYJNAPOPMIJKJZ-UHFFFAOYSA-N 0.000 description 5
- 239000002243 precursor Substances 0.000 description 5
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
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- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 239000005639 Lauric acid Substances 0.000 description 3
- ZDZOTLJHXYCWBA-VCVYQWHSSA-N N-debenzoyl-N-(tert-butoxycarbonyl)-10-deacetyltaxol Chemical compound O([C@H]1[C@H]2[C@@](C([C@H](O)C3=C(C)[C@@H](OC(=O)[C@H](O)[C@@H](NC(=O)OC(C)(C)C)C=4C=CC=CC=4)C[C@]1(O)C3(C)C)=O)(C)[C@@H](O)C[C@H]1OC[C@]12OC(=O)C)C(=O)C1=CC=CC=C1 ZDZOTLJHXYCWBA-VCVYQWHSSA-N 0.000 description 3
- BZQFBWGGLXLEPQ-UHFFFAOYSA-N O-phosphoserine Chemical compound OC(=O)C(N)COP(O)(O)=O BZQFBWGGLXLEPQ-UHFFFAOYSA-N 0.000 description 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- 239000013543 active substance Substances 0.000 description 3
- 125000002252 acyl group Chemical group 0.000 description 3
- 229930013930 alkaloid Natural products 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- DBXFAPJCZABTDR-WBYYIXQISA-N cephalomannine Chemical compound O([C@@H]1[C@]2(O)C[C@@H](C(=C([C@@H](OC(C)=O)C(=O)[C@]3(C)[C@@H](O)C[C@H]4OC[C@]4([C@H]31)OC(C)=O)C2(C)C)C)OC(=O)[C@H](O)[C@@H](NC(=O)C(/C)=C/C)C=1C=CC=CC=1)C(=O)C1=CC=CC=C1 DBXFAPJCZABTDR-WBYYIXQISA-N 0.000 description 3
- WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 3
- 235000012000 cholesterol Nutrition 0.000 description 3
- 230000008878 coupling Effects 0.000 description 3
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- 238000005859 coupling reaction Methods 0.000 description 3
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
- 230000000144 pharmacologic effect Effects 0.000 description 3
- 239000008389 polyethoxylated castor oil Substances 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- 230000004083 survival effect Effects 0.000 description 3
- 150000004579 taxol derivatives Chemical class 0.000 description 3
- 229940063683 taxotere Drugs 0.000 description 3
- 231100001274 therapeutic index Toxicity 0.000 description 3
- 238000011282 treatment Methods 0.000 description 3
- YWLXLRUDGLRYDR-ZHPRIASZSA-N 5beta,20-epoxy-1,7beta,10beta,13alpha-tetrahydroxy-9-oxotax-11-ene-2alpha,4alpha-diyl 4-acetate 2-benzoate Chemical compound O([C@H]1[C@H]2[C@@](C([C@H](O)C3=C(C)[C@@H](O)C[C@]1(O)C3(C)C)=O)(C)[C@@H](O)C[C@H]1OC[C@]12OC(=O)C)C(=O)C1=CC=CC=C1 YWLXLRUDGLRYDR-ZHPRIASZSA-N 0.000 description 2
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 102000004243 Tubulin Human genes 0.000 description 2
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- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
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- YZXBAPSDXZZRGB-DOFZRALJSA-N arachidonic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O YZXBAPSDXZZRGB-DOFZRALJSA-N 0.000 description 2
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- 239000004020 conductor Substances 0.000 description 2
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- NQGIJDNPUZEBRU-UHFFFAOYSA-N dodecanoyl chloride Chemical compound CCCCCCCCCCCC(Cl)=O NQGIJDNPUZEBRU-UHFFFAOYSA-N 0.000 description 2
- 239000003925 fat Substances 0.000 description 2
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- OVBPIULPVIDEAO-LBPRGKRZSA-N folic acid Chemical compound C=1N=C2NC(N)=NC(=O)C2=NC=1CNC1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 OVBPIULPVIDEAO-LBPRGKRZSA-N 0.000 description 2
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Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B82—NANOTECHNOLOGY
- B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
- B82Y5/00—Nanobiotechnology or nanomedicine, e.g. protein engineering or drug delivery
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/10—Dispersions; Emulsions
- A61K9/127—Liposomes
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D305/00—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms
- C07D305/14—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms condensed with carbocyclic rings or ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/655—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms
- C07F9/6551—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms the oxygen atom being part of a four-membered ring
- C07F9/65512—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms the oxygen atom being part of a four-membered ring condensed with carbocyclic rings or carbocyclic ring systems
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Molecular Biology (AREA)
- Nanotechnology (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- General Engineering & Computer Science (AREA)
- Dispersion Chemistry (AREA)
- Biochemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biophysics (AREA)
- Biotechnology (AREA)
- Medical Informatics (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Epoxy Compounds (AREA)
- Medicinal Preparation (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US36981795A | 1995-01-09 | 1995-01-09 | |
| US08/369,817 | 1995-01-09 | ||
| US08/474,888 US5580899A (en) | 1995-01-09 | 1995-06-07 | Hydrophobic taxane derivatives |
| US08/474,888 | 1995-06-07 | ||
| PCT/US1996/000351 WO1996021658A1 (en) | 1995-01-09 | 1996-01-11 | Hydrophobic taxane derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH11500712A true JPH11500712A (ja) | 1999-01-19 |
Family
ID=27004714
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP8521801A Ceased JPH11500712A (ja) | 1995-01-09 | 1996-01-11 | 疎水性タキサン誘導体 |
Country Status (13)
| Country | Link |
|---|---|
| US (4) | US5580899A (da) |
| EP (2) | EP0802911B1 (da) |
| JP (1) | JPH11500712A (da) |
| KR (1) | KR100386002B1 (da) |
| AT (2) | ATE209196T1 (da) |
| AU (1) | AU691401B2 (da) |
| CA (1) | CA2209001C (da) |
| DE (3) | DE69627722T2 (da) |
| DK (2) | DK1063234T3 (da) |
| ES (2) | ES2154622T3 (da) |
| GR (1) | GR20010300005T1 (da) |
| PT (2) | PT1063234E (da) |
| WO (1) | WO1996021658A1 (da) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2008529745A (ja) * | 2005-02-18 | 2008-08-07 | アブラクシス バイオサイエンス、インコーポレイテッド | 医療装置に結合した改善された疎水性を有した薬剤 |
| JP2019532973A (ja) * | 2016-10-28 | 2019-11-14 | レ ラボラトワール セルヴィエ | ガンの処置において使用するためのリポソーム製剤 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20030068362A1 (en) * | 1993-02-22 | 2003-04-10 | American Bioscience, Inc. | Methods and formulations for the delivery of pharmacologically active agents |
| US5580899A (en) * | 1995-01-09 | 1996-12-03 | The Liposome Company, Inc. | Hydrophobic taxane derivatives |
| US6107332A (en) | 1995-09-12 | 2000-08-22 | The Liposome Company, Inc. | Hydrolysis-promoting hydrophobic taxane derivatives |
| EP1229030B1 (en) * | 1995-09-12 | 2005-11-09 | Zeneus Pharma Limited | Hydrolysis-promoting taxane hydrophobic derivates |
| JP4192208B2 (ja) * | 1995-09-12 | 2008-12-10 | セファロン リミテッド | 加水分解促進性のタキサン疎水性誘導体 |
| US6667053B1 (en) * | 1996-02-16 | 2003-12-23 | Elan Pharmaceuticals, Inc. | D and L etherlipid stereoisomers and liposomes |
| US6441025B2 (en) * | 1996-03-12 | 2002-08-27 | Pg-Txl Company, L.P. | Water soluble paclitaxel derivatives |
| US5919815A (en) * | 1996-05-22 | 1999-07-06 | Neuromedica, Inc. | Taxane compounds and compositions |
| JP4172726B2 (ja) * | 1996-05-22 | 2008-10-29 | ルイトポルド・ファーマシューティカルズ・インコーポレーテッド | シス―ドコサヘキサエン酸とドセタキセルとの共有複合体を含有する製剤 |
| US6576636B2 (en) | 1996-05-22 | 2003-06-10 | Protarga, Inc. | Method of treating a liver disorder with fatty acid-antiviral agent conjugates |
| US5795909A (en) * | 1996-05-22 | 1998-08-18 | Neuromedica, Inc. | DHA-pharmaceutical agent conjugates of taxanes |
| NZ505584A (en) | 1996-05-24 | 2002-04-26 | Univ British Columbia | Delivery of a therapeutic agent to the smooth muscle cells of a body passageway via an adventia |
| GB2321455A (en) * | 1997-01-24 | 1998-07-29 | Norsk Hydro As | Lipophilic derivatives of biologically active compounds |
| US7112338B2 (en) * | 1997-03-12 | 2006-09-26 | The Regents Of The University Of California | Cationic liposome delivery of taxanes to angiogenic blood vessels |
| US5837283A (en) * | 1997-03-12 | 1998-11-17 | The Regents Of The University Of California | Cationic lipid compositions targeting angiogenic endothelial cells |
| US6136988A (en) * | 1998-04-10 | 2000-10-24 | Hauser, Inc. | 7-hexanoyltaxol and methods for preparing the same |
| US6461637B1 (en) * | 2000-09-01 | 2002-10-08 | Neopharm, Inc. | Method of administering liposomal encapsulated taxane |
| US6146659A (en) * | 1998-07-01 | 2000-11-14 | Neopharm, Inc. | Method of administering liposomal encapsulated taxane |
| US7314637B1 (en) | 1999-06-29 | 2008-01-01 | Neopharm, Inc. | Method of administering liposomal encapsulated taxane |
| US6136989A (en) * | 1998-12-30 | 2000-10-24 | Phytogen Life Sciences, Incorporated | Method for high yield and large scale extraction of paclitaxel from paclitaxel-containing material |
| ATE297198T1 (de) * | 1999-02-23 | 2005-06-15 | Angiotech Int Ag | Zusammensetzungen und verfahren zur verbesserung der integrität von angegriffenen körperpassagewegen und höhlen |
| US6191290B1 (en) * | 1999-02-24 | 2001-02-20 | Uab Research Foundation | Taxane derivatives for targeted therapy of cancer |
| KR20020000147A (ko) * | 1999-03-09 | 2002-01-04 | 니겔 엘. 웹 | 지방산-항암제 결합체 및 그의 용도 |
| US7235583B1 (en) * | 1999-03-09 | 2007-06-26 | Luitpold Pharmaceuticals, Inc., | Fatty acid-anticancer conjugates and uses thereof |
| WO2000067802A1 (en) * | 1999-05-10 | 2000-11-16 | Protarga, Inc. | Fatty acid-n-substituted indol-3-glyoxyl-amide compositions and uses thereof |
| HUP0202669A3 (en) * | 1999-09-09 | 2004-06-28 | Univ California | Cationic liposome delivery of taxanes to angiogenic bloos vessels |
| CA2385528C (en) | 1999-10-01 | 2013-12-10 | Immunogen, Inc. | Compositions and methods for treating cancer using immunoconjugates and chemotherapeutic agents |
| US6362217B2 (en) * | 2000-03-17 | 2002-03-26 | Bristol-Myers Squibb Company | Taxane anticancer agents |
| EP1423107B1 (en) | 2001-03-23 | 2012-05-09 | Luitpold Pharmaceuticals, Inc. | Fatty alcohol drug conjugates |
| US8552054B2 (en) | 2001-03-23 | 2013-10-08 | Luitpold Pharmaceuticals, Inc. | Fatty amine drug conjugates |
| CA2445763A1 (en) * | 2001-05-01 | 2002-11-07 | Angiotech Pharmaceuticals Inc. | Compositions comprising an anti-microtubule agent and a polypeptide or a polysaccharide and the use thereof for the preparation of a medicament for the treatment of inflammatory conditions |
| US20030157161A1 (en) * | 2001-05-01 | 2003-08-21 | Angiotech Pharmaceuticals, Inc. | Compositions and methods for treating inflammatory conditions utilizing protein or polysaccharide containing anti-microtubule agents |
| DE10154464B4 (de) * | 2001-11-08 | 2005-10-20 | Max Delbrueck Centrum | Oral verabreichbare pharmazeutische Zubereitung umfassend liposomal verkapseltes Taxol |
| US20030206893A1 (en) * | 2002-05-06 | 2003-11-06 | Sohail Malik | Cell proliferating agents |
| WO2004069224A2 (en) | 2003-02-03 | 2004-08-19 | Neopharm, Inc. | Stable sterile filterable liposomal encapsulated taxane and other antineoplastic drugs |
| JP2006248978A (ja) * | 2005-03-10 | 2006-09-21 | Mebiopharm Co Ltd | 新規なリポソーム製剤 |
| WO2006110862A2 (en) * | 2005-04-12 | 2006-10-19 | Wisconsin Alumni Research Foundation | Micelle composition of polymer and passenger drug |
| EP1883627B1 (en) | 2005-05-18 | 2018-04-18 | Pharmascience Inc. | Bir domain binding compounds |
| NZ572836A (en) | 2006-05-16 | 2011-12-22 | Pharmascience Inc | Iap bir domain binding compounds |
| ES2535217T3 (es) * | 2007-11-28 | 2015-05-07 | Celator Pharmaceuticals, Inc. | Sistema mejorado de administración de taxano |
| AU2009234127B2 (en) * | 2008-04-10 | 2015-04-30 | Abraxis Bioscience, Llc | Compositions of hydrophobic taxane derivatives and uses thereof |
| WO2011038278A2 (en) | 2009-09-25 | 2011-03-31 | Wisconsin Alumni Research Foundation | Micelle encapsulation of therapeutic agents |
| SG10201501095WA (en) | 2010-02-12 | 2015-04-29 | Pharmascience Inc | Iap bir domain binding compounds |
| TWI438009B (zh) * | 2010-02-19 | 2014-05-21 | Teikoku Pharma Usa Inc | 紫杉烷前－乳劑調配物及其製造與使用之方法 |
| CN103096874A (zh) * | 2010-04-15 | 2013-05-08 | 华盛顿大学 | 前药组合物、前药纳米粒子及其使用方法 |
| EP2566474B1 (en) | 2010-05-03 | 2017-11-15 | Teikoku Pharma USA, Inc. | Non-aqueous taxane pro-emulsion formulations and methods of making and using the same |
| PL226015B1 (pl) | 2011-03-03 | 2017-06-30 | Wrocławskie Centrum Badań Eit + Spółka Z Ograniczoną | Liposomowy preparat zawierajacy przeciwnowotworowa substancje aktywna, sposob jego wytwarzania i zawierajaca go kompozycja farmaceutyczna |
| US8945627B2 (en) | 2011-05-05 | 2015-02-03 | Wisconsin Alumni Research Foundation | Micelles for the solubilization of gossypol |
| US20140357706A1 (en) * | 2011-10-13 | 2014-12-04 | The Uab Research Foundation | Stearate Compounds |
| JO3685B1 (ar) | 2012-10-01 | 2020-08-27 | Teikoku Pharma Usa Inc | صيغ التشتيت الجسيمي للتاكسين غير المائي وطرق استخدامها |
| US10682415B2 (en) | 2013-07-22 | 2020-06-16 | Wisconsin Alumni Research Foundation | Thermogel formulation for combination drug delivery |
| CN105853403B (zh) * | 2016-05-09 | 2019-03-29 | 上海天氏利医药科技有限公司 | 一种紫杉醇棕榈酸酯脂质体及其制备方法 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4960790A (en) * | 1989-03-09 | 1990-10-02 | University Of Kansas | Derivatives of taxol, pharmaceutical compositions thereof and methods for the preparation thereof |
| CA2023645C (fr) * | 1989-08-23 | 2002-03-26 | Jean-Noel Denis | Procede pour la preparation enantioselective de derives de la phenylisoserine |
| US5015744A (en) * | 1989-11-14 | 1991-05-14 | Florida State University | Method for preparation of taxol using an oxazinone |
| FR2658510B1 (fr) * | 1990-02-21 | 1992-04-30 | Rhone Poulenc Sante | Nouveau derive de la beta-phenylisoserine, sa preparation et son emploi. |
| FR2678930B1 (fr) * | 1991-07-10 | 1995-01-13 | Rhone Poulenc Rorer Sa | Procede de preparation de derives de la baccatine iii et de la desacetyl-10 baccatine iii. |
| FR2680506B1 (fr) * | 1991-08-19 | 1994-09-02 | Rhone Poulenc Rorer Sa | Procede de preparation de derives de la beta-phenylisoserine et leur utilisation. |
| WO1993010076A1 (en) * | 1991-11-22 | 1993-05-27 | The University Of Mississippi | Synthesis and optical resolution of the taxol side chain and related compounds |
| FR2687150B1 (fr) * | 1992-02-07 | 1995-04-28 | Rhone Poulenc Rorer Sa | Procede de preparation de derives du taxane. |
| US5272171A (en) * | 1992-02-13 | 1993-12-21 | Bristol-Myers Squibb Company | Phosphonooxy and carbonate derivatives of taxol |
| US5200534A (en) * | 1992-03-13 | 1993-04-06 | University Of Florida | Process for the preparation of taxol and 10-deacetyltaxol |
| US5534499A (en) * | 1994-05-19 | 1996-07-09 | The University Of British Columbia | Lipophilic drug derivatives for use in liposomes |
| US5580899A (en) * | 1995-01-09 | 1996-12-03 | The Liposome Company, Inc. | Hydrophobic taxane derivatives |
-
1995
- 1995-06-07 US US08/474,888 patent/US5580899A/en not_active Expired - Lifetime
-
1996
- 1996-01-11 DE DE69627722T patent/DE69627722T2/de not_active Expired - Fee Related
- 1996-01-11 CA CA002209001A patent/CA2209001C/en not_active Expired - Fee Related
- 1996-01-11 JP JP8521801A patent/JPH11500712A/ja not_active Ceased
- 1996-01-11 ES ES00121129T patent/ES2154622T3/es not_active Expired - Lifetime
- 1996-01-11 ES ES96903428T patent/ES2163613T3/es not_active Expired - Lifetime
- 1996-01-11 AT AT96903428T patent/ATE209196T1/de not_active IP Right Cessation
- 1996-01-11 DE DE1063234T patent/DE1063234T1/de active Pending
- 1996-01-11 WO PCT/US1996/000351 patent/WO1996021658A1/en active IP Right Grant
- 1996-01-11 PT PT00121129T patent/PT1063234E/pt unknown
- 1996-01-11 KR KR1019970704678A patent/KR100386002B1/ko not_active IP Right Cessation
- 1996-01-11 DK DK00121129T patent/DK1063234T3/da active
- 1996-01-11 DK DK96903428T patent/DK0802911T3/da active
- 1996-01-11 DE DE69617203T patent/DE69617203T2/de not_active Expired - Fee Related
- 1996-01-11 AU AU47522/96A patent/AU691401B2/en not_active Ceased
- 1996-01-11 PT PT96903428T patent/PT802911E/pt unknown
- 1996-01-11 EP EP96903428A patent/EP0802911B1/en not_active Expired - Lifetime
- 1996-01-11 AT AT00121129T patent/ATE238290T1/de not_active IP Right Cessation
- 1996-01-11 EP EP00121129A patent/EP1063234B1/en not_active Expired - Lifetime
- 1996-11-27 US US08/753,650 patent/US6118011A/en not_active Expired - Fee Related
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1997
- 1997-12-10 US US08/988,120 patent/US5939567A/en not_active Expired - Fee Related
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2000
- 2000-05-09 US US09/567,366 patent/US6291690B1/en not_active Expired - Fee Related
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2001
- 2001-02-28 GR GR20010300005T patent/GR20010300005T1/el unknown
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2008529745A (ja) * | 2005-02-18 | 2008-08-07 | アブラクシス バイオサイエンス、インコーポレイテッド | 医療装置に結合した改善された疎水性を有した薬剤 |
| JP2019532973A (ja) * | 2016-10-28 | 2019-11-14 | レ ラボラトワール セルヴィエ | ガンの処置において使用するためのリポソーム製剤 |
Also Published As
| Publication number | Publication date |
|---|---|
| EP1063234A2 (en) | 2000-12-27 |
| AU4752296A (en) | 1996-07-31 |
| ES2163613T3 (es) | 2002-02-01 |
| DE69627722T2 (de) | 2003-10-16 |
| PT802911E (pt) | 2002-05-31 |
| AU691401B2 (en) | 1998-05-14 |
| US5580899A (en) | 1996-12-03 |
| US6291690B1 (en) | 2001-09-18 |
| WO1996021658A1 (en) | 1996-07-18 |
| US6118011A (en) | 2000-09-12 |
| EP0802911A1 (en) | 1997-10-29 |
| CA2209001C (en) | 2007-12-18 |
| DE69617203D1 (de) | 2002-01-03 |
| EP0802911B1 (en) | 2001-11-21 |
| DK1063234T3 (da) | 2003-06-02 |
| ATE238290T1 (de) | 2003-05-15 |
| DE69627722D1 (de) | 2003-05-28 |
| EP1063234B1 (en) | 2003-04-23 |
| EP1063234A3 (en) | 2001-04-11 |
| DE1063234T1 (de) | 2001-05-23 |
| ATE209196T1 (de) | 2001-12-15 |
| US5939567A (en) | 1999-08-17 |
| ES2154622T3 (es) | 2003-09-16 |
| ES2154622T1 (es) | 2001-04-16 |
| CA2209001A1 (en) | 1996-07-18 |
| PT1063234E (pt) | 2003-09-30 |
| KR19980701289A (ko) | 1998-05-15 |
| DK0802911T3 (da) | 2002-05-21 |
| GR20010300005T1 (en) | 2001-02-28 |
| DE69617203T2 (de) | 2002-05-08 |
| KR100386002B1 (ko) | 2003-10-10 |
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